In this episode, Jacob Winograd takes on Jon Stewart’s infamous “19 Questions for Libertarians” from his 2011 exchange with Judge Napolitano. Stewart’s list of “gotcha” questions—about roads, firemen, safety nets, and “heartless” libertarians—once made waves online. But more than a decade later, Jacob unpacks why those same arguments still miss the mark.

From a distinctly biblical libertarian perspective, Jacob answers each question one by one, exposing the hidden assumptions behind them and showing that true compassion doesn’t come from coercion. He breaks down what liberty really means, why government isn’t the source of rights, and how biblical principles of justice, charity, and personal responsibility offer a better foundation for a free and moral society.

Full Episode Notes at BiblicalAnarchyPodcast.com

The Biblical Anarchy Podcast is part of the Christians For Liberty Network, a project of the Libertarian Christian Institute.

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What does it really mean when Christians declare, “Christ is King”—and how does that truth confront the kingdoms of this world? In this episode, Jacob Winograd welcomes Christian anarchist songwriter Ancap Tim, whose new album The State Is a Mafia challenges believers to rethink their allegiance, patriotism, and the nature of true authority. Tim shares his remarkable journey from a “Bush-cake conservative” and Republican loyalist to a libertarian anarchist shaped by Ron Paul’s message of peace and sound money. Together, he and Jacob explore how faith and liberty meet in music, from parodying Billy Joel in We Didn’t Start the Scheming to proclaiming No King But Christ as an anthem of spiritual rebellion against state idolatry.

Their conversation dives deep into how modern churches have blurred the line between worship and nationalism, the corruption of banking and empire, and the difference between coercion and voluntary cooperation. They also unpack the moral roots of pacifism and self-defense, the call to resist through creativity and community, and why living under Christ’s reign now means rejecting Caesar’s counterfeit power. Whether you’re curious about Christian anarchism, the theology behind “Christ is King,” or simply love music that speaks truth to power, this episode is both challenging and inspiring.

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Inflation isn’t just an economic issue—it’s a spiritual one. In this episode, Jacob Winograd and economist Dr. Jeffrey Degner expose how the Federal Reserve’s inflationary system quietly undermines biblical principles, fosters sin, and tears at the fabric of family life. From dishonest scales to debt slavery, they uncover the moral and social fallout of modern central banking.

Full Episode Notes at BiblicalAnarchyPodcast.com

The Biblical Anarchy Podcast is part of the Christians For Liberty Network, a project of the Libertarian Christian Institute.

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In this bonus episode of the Biblical Anarchy Podcast, Jacob republishes his appearance on The Libertarian Christian Podcast with host Cody Cook and fellow guest Chris Todd, a missionary and trauma therapist based in the Middle East. The conversation begins with Chris sharing firsthand accounts of working with war-torn communities in Lebanon and Syria, offering insight into the human side of conflict and the deep wounds left by war, displacement, and oppression. These personal stories set the stage for a broader discussion on how Christians should understand the ongoing Israel-Palestine conflict through the lens of faith, justice, and compassion.

The dialogue then turns toward theology, examining how covenant theology provides a Christ-centered framework for understanding God’s promises in contrast to dispensationalist approaches. Jacob explains how the covenants throughout Scripture point toward fulfillment in Christ, while Chris highlights how misreadings of Scripture often distort political support for the modern state of Israel. Together, the panel unpacks how theology shapes Christian engagement with issues of war, nationalism, and antisemitism, calling believers back to the peace of Christ as the true hope for both Israelis and Palestinians.

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In this episode of The Greenroom, Jacob Winograd is joined by Nikki Phillippi, a longtime YouTuber, musician, and outspoken Christian whose career has been marked by both influence and controversy. Nikki shares her story of navigating the highs and lows of public life — from early success in music and lifestyle content, to the painful seasons of backlash over adoption, her stance on COVID, and the loss of friendships along the way. Through it all, she has sought to remain unashamed of the gospel, even when speaking biblical truth came at the cost of her reputation.

The conversation ranges widely: Nikki reflects on her upbringing and her father’s powerful conversion, the way homeschooling and motherhood reshaped her view of family, and why she believes cancel culture often reveals the idols of our age. Jacob and Nikki also dive into conspiracies, child trafficking, and the dangers of the entertainment industry, before turning to bigger questions about politics, liberty, and the role of faith in resisting a hostile culture. By the end, listeners will come away with a raw and relatable picture of what it means to live freely in Christ while pushing back against both cultural pressure and political overreach.

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In this episode of the Biblical Anarchy Podcast, host Jacob Winograd takes the well-known Political Compass quiz and works through each question in real time. Instead of just clicking answers, he explains how a Christian libertarian frames the issues—separating what is sinful from what is criminal, exposing false choices, and keeping the focus on justice and neighbor-love rather than partisan labels. He also calls out the quiz’s built-in assumptions, like the way it blurs economic freedom with political centralization or equates patriotism with blind loyalty to the state.

Across the conversation, Jacob applies core principles like self-ownership and the non-aggression principle to a wide range of issues: free trade, abortion, war, the environment, drug laws, corporate power, and more. He emphasizes that government’s job isn’t to police all immorality but to protect against aggression, a distinction many political models miss. By the end, the results page matters less than the exercise itself—showing how Christians can think clearly about politics without getting trapped in the left-right binary or letting Caesar define the terms of the debate.

Full Episode Notes at BiblicalAnarchyPodcast.com

The Biblical Anarchy Podcast is part of the Christians For Liberty Network, a project of the Libertarian Christian Institute.

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In this episode of the Biblical Anarchy Podcast, host Jacob Winograd sits down with RT Hadley, a 20-year Air Force veteran turned Christian writer, to wrestle with the difficult question: Has the United States ever fought a truly just war? Drawing from Hadley’s military service in Iraq, his spiritual reflections, and his studies on just war theory, the two explore how patriotism, faith, and war collide in the American story. Together they consider the church’s entanglement with empire, the writings of Augustine and Aquinas, and how Christians today can faithfully engage politics without compromising spiritual integrity.

The conversation traces Hadley’s personal journey from neoconservatism to libertarian anti-interventionism, examining the moral weight of war through the lens of both history and Scripture. Topics include the Revolutionary War, America’s modern interventions, Christian nationalism, and the enduring call of Christ to love neighbor and enemy alike. This dialogue is both challenging and pastoral, calling believers to discern where loyalty to Caesar ends and faithfulness to Christ begins.

Full Episode Notes at BiblicalAnarchyPodcast.com

The Biblical Anarchy Podcast is part of the Christians For Liberty Network, a project of the Libertarian Christian Institute.

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In this episode of the Biblical Anarchy Podcast, Jacob Winograd sits down with returning guest Kerry Baldwin to take on a question many Christians wrestle with: if people are sinful, doesn’t that mean we need the state? Drawing on Baldwin’s long-standing work on the plausibility of stateless civil governance, the two tackle this objection head-on and show why handing unchecked power to sinners creates even greater injustice.

Their conversation digs into John Locke’s classic arguments for monopolistic civil government (the State) and turns them on their head, showing how impartial judges, clear laws, and effective enforcement actually point toward a polycentric order rather than a state monopoly. Along the way, they revisit the biblical principle of sphere sovereignty, explore how justice works in practice without centralized control, and push back on the idea that the state is inevitable. The discussion closes with practical reflections for Christians and libertarians on how to live out these principles now—through entrepreneurship, grassroots action, and faith in Christ’s ultimate kingship.

Full Episode Notes at BiblicalAnarchyPodcast.com

The Biblical Anarchy Podcast is part of the Christians For Liberty Network, a project of the Libertarian Christian Institute.

Audio Production by Podsworth Media.